Pd-Catalyzed Highly Regio- and Stereoselective Formation of C-C Double Bonds: An Efficient Method for the Synthesis of Benzofuran-, Dihydrobenzofuran-, and Indoline-Containing Alkenes

被引：72

作者：

Gao, Yang ^{[1
]}

Xiong, Wenfang ^{[1
]}

Chen, Huoji ^{[1
]}

Wu, Wanqing ^{[1
]}

Peng, Jianwen ^{[1
]}

Gao, Yinglan ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 15期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; N-TOSYL HYDRAZONES; OXIDATIVE ADDITION; DIAZO-COMPOUNDS; 3-COMPONENT REACTION; MIGRATORY INSERTION; SELECTIVE SYNTHESIS; CASCADE REACTIONS; OLEFIN SYNTHESIS; METAL CARBENE;

D O I：

10.1021/acs.joc.5b01024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regio- and stereoselective C-C double bond formation reaction via Pd-catalyzed Heck-type cascade process with N-tosylhydrazones has been developed. Various N-tosylhydrazones derived from both ketones and aldehydes are found to be efficient substrates to provide di- and trisubstituted olefins with high regio- and stereoselectivity. Furthermore, this reaction has a good functional group tolerance and different benzofuran-, dihydrobenzofuran-, and indoline-containing alkene products were obtained with high selectivity.

引用

页码：7456 / 7467

页数：12

共 66 条

[1] INTRAMOLECULAR ALKENE ARYLATIONS FOR RAPID ASSEMBLY OF POLYCYCLIC SYSTEMS CONTAINING QUATERNARY CENTERS - A NEW SYNTHESIS OF SPIROOXINDOLES AND OTHER FUSED AND BRIDGED RING-SYSTEMS [J].

ABELMAN, MM ;

OH, T ;

OVERMAN, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4130-4133

[2] Antiangiogenic activity of synthetic dihydrobenzofuran lignans [J].

Apers, S ;

Paper, D ;

Bürgermeister, J ;

Baronikova, S ;

Van Dyck, S ;

Lemière, G ;

Vlietinck, A ;

Pieters, L .

JOURNAL OF NATURAL PRODUCTS, 2002, 65 (05) :718-720

[3] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins [J].

Barluenga, José ;

Moriel, Patricia ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5587-5590

[4] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[5] Tosylhydrazide-Promoted Palladium-Catalyzed Reaction of β-Aminoketones with o-Dihaloarenes: Combining Organocatalysis and Transition-Metal Catalysis [J].

Barluenga, Jose ;

Quinones, Noelia ;

Cabal, Maria-Paz ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2350-2353

[6] Synthesis of Polysubstituted Olefins by Pd-Catalyzed Cross-Coupling Reaction of Tosylhydrazones and Aryl Nonaflates [J].

Barluenga, Jose ;

Florentino, Lucia ;

Aznar, Fernando ;

Valdes, Carlos .

ORGANIC LETTERS, 2011, 13 (03) :510-513

[7] Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides [J].

Barluenga, Jose ;

Escribano, Maria ;

Aznar, Fernando ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) :6856-6859

[8] Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions [J].

Barluenga, Jose ;

Escribano, Maria ;

Moriel, Patricia ;

Aznar, Fernando ;

Valdes, Carlos .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) :13291-13294

[9] CC-1065 and the duocarmycins: Synthetic studies [J].

Boger, DL ;

Boyce, CW ;

Garbaccio, RM ;

Goldberg, JA .

CHEMICAL REVIEWS, 1997, 97 (03) :787-828

[10] Approaches to the quaternary stereocentre and to the heterocyclic core in diazonamide A using the Heck reaction and related coupling reactions [J].

Booker, James E. M. ;

Boto, Alicia ;

Churchill, Gwydion H. ;

Green, Clive P. ;

Ling, Matthew ;

Meek, Graham ;

Prabhakaran, Jaya ;

Sinclair, David ;

Blake, Alexander J. ;

Pattenden, Gerald .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4193-4205

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